tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane

Base Information

• Chemical Name: tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane
• CAS No.: 1374851-79-2
• Molecular Formula: C₄₆H₅₅FO₄Si₂
• Molecular Weight: 747.11

Synonyms:tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane

Chemical Property of tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane

Chemical Property:

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Technology Process of tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane

There total 13 articles about tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methanol (1374851-78-1) + tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane (1374851-79-2)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tet.2012.03.023

Reference yield:

(3aS,4S,6R,6aR)-4-(4-methoxybenzyloxy)-6-vinyltetrahydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentane] (1009810-93-8) → tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane (1374851-79-2)

Guidance literature:

Multi-step reaction with 8 steps

1: hydrogenchloride / methanol / 25 °C

2: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / -40 - 60 °C

4: lithium hydroxide / methanol / 2 h / 25 °C

5: pyridine; diethylamino-sulfur trifluoride / dichloromethane / 12 h / 20 °C / Inert atmosphere

6: sodium periodate; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / methanol / 2 h / 0 °C

7: methanol; sodium tetrahydroborate / 1 h / 0 °C

8: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; diethylamino-sulfur trifluoride; di-isopropyl azodicarboxylate; water; 4-methylmorpholine N-oxide; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 3: Mitsunobu reaction;

DOI:10.1016/j.tet.2012.03.023

Reference yield:

(3aR,6R,6aR)-6-vinyldihydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-4(6aH)-one (1374851-71-4) → tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane (1374851-79-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate / 1 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

2.2: 3 h / 0 - 20 °C

3.1: hydrogenchloride / methanol / 25 °C

4.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / -40 - 60 °C

6.1: lithium hydroxide / methanol / 2 h / 25 °C

7.1: pyridine; diethylamino-sulfur trifluoride / dichloromethane / 12 h / 20 °C / Inert atmosphere

8.1: sodium periodate; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / methanol / 2 h / 0 °C

9.1: methanol; sodium tetrahydroborate / 1 h / 0 °C

10.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; diethylamino-sulfur trifluoride; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; water; sodium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil; 5.1: Mitsunobu reaction;

DOI:10.1016/j.tet.2012.03.023

upstream raw materials:

(3aS,4S,6R,6aR)-4-(4-methoxybenzyloxy)-6-vinyltetrahydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentane]

1-((2S,3R)-3-vinyl-1,4-dioxaspiro[4.4]nonan-2-yl)prop-2-en-1-ol

(3aR,6aR)-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-4(6aH)-one

(3aR,6R,6aR)-6-vinyldihydro-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-4(6aH)-one

Downstream raw materials:

(1S,2S,3R,4R)-3-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-fluorocyclopentanol

1-((1R,2S,3R,4R)-3-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-fluorocyclopentyl)-4-(N,N-di(tert-butyloxycarbonyl)amino)-1H-imidazo[4,5-c]pyridine

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